New to Online Dating? What I Wish Someone Had Told Me

3 minute read

By: Jill Waldbieser|Last updated: October 17, 2022
Woman smiling in sunglasses being kissed on the cheek by bearded man at beach. AW323

Online dating is like visiting the Grand Canyon: You can hear about it from friends, read guidebooks, and plan out every detail for yourself, but nothing quite prepares you for the stark reality of how you’ll feel once you’re actually staring into the abyss. Or just how bottomless it seems.

I had delayed downloading dating apps for years, dreading the thought of dealing with the ghosting, the scamming, the endless barrage of unwanted dick pics. But this year, I finally gave in to the inevitable. After all, research shows that social circles tend to shrink as we age, and the pandemic’s butterfly effect hasn’t exactly made meeting new people any easier. 

In my inexperience, I was convinced I had this in the bag. I was well-versed in safety protocol, text messaging is my preferred means of communication, I’m decently photogenic (as is my dog), and working in media, I know how to brand myself. Plus, I’d heard that as a woman, I’d basically just be weeding through profiles of men begging to go out with me, as effortless as an HR recruiter for Ben & Jerry’s flavor testers. I envisioned a full social calendar and some great stories. 

Instead, I deleted all the apps within a month, without ever having an actual in-person date. The catalyst? After months of texting and trying to set up an in-person meeting around my custody schedule and his job’s near-constant travel itinerary me and my latest match finally had a free weekend. This sounds promising, but for me it had often been the stage where things fall apart when I realize I’m expected to plan the entire date—no thanks. 

But this fellow took initiative. A little too much initiative. Because his car was in a carpark in another state, where he’d left it before his latest business flight, he suggested he just get a hotel in my town and have me chauffeur him around. I thought he was joking, but as soon as I realized he was not, told him that was way too much pressure for a first date and I had been thinking something like coffee or brunch. I even suggested a place I’d been wanting to go that was midway between us. I woke up the next morning to a text that he had gone ahead and gotten a hotel, and he was there now, did I want to get breakfast? 

I was incredulous, then extremely uneasy. I hardly wanted to leave the house, even to walk my dog. My mind flashed back to how easily he had googled me before I had even given him my last name (apparently a search of my profession and county in which I live is plenty) and how he commented on things that would have required deep, deep scrolling in my IG feed. I finally replied to his text that him ignoring my clearly stated wishes not to book a hotel made me very uncomfortable, and I no longer wanted to meet now, or ever. I got a response telling me to “get over myself.” And back into the dating pool this 40-something-year-old man splashed, still believing that booking a hotel room for a first date with a total stranger against her stated wishes is entirely appropriate behavior. The pool is stocked with similar species.

I think I handled myself well, but I do wish I had been better prepared for the realities of online dating later in life before I ever made my first profile. Realties like:

Start with the right mindset. “After a breakup, a lot of people download six apps and get overwhelmed,” says Melissa Fulgieri, LCSW, a New York-based relationship therapist.

Though I cringe to admit it, this was me. I felt like my life was stable and I desperately wanted to move on and date, but emotionally, I just wasn’t ready to deal with the frustration, confusion, and just plain gross behavior of online dating. “The thing with apps is, no one has to treat you like a human if they don’t want to,” Fulgieri says. Indeed, that could be why one 2021 study found that users of online dating have higher rates of depression and social anxiety. “You have to think about your mental health and how you’ll feel knowing it’s a jungle out there.”

Set healthy limits. No matter which app you use, it’s important to remember they are all designed to be addictive to keep you coming back, says Fulgieri. I found this out firsthand when my careful plan to set aside 15 minutes a day for online dating went out the window as I compulsively swiped past midnight, then checked if there had been any action immediately upon waking.  Turning off notifications can help, but remember, “No one is going to put those boundaries in but you,” Fulgieri says. She suggests doing a self-inventory on a regular basis to ask yourself, How is this making me feel? How much time am I spending on this versus other things in my life? 

Choose the right app. Some apps have a rep for quick hookups, others are better known for launching meaningful relationships. Dating Scout actually ranks and reviews some of them, but even a quick online search can give you some idea of what may be the best fit for you. There are also several newer apps testing a model that isn’t as mired in physical appearance and geographic location algorithms, things like Coffee Meets Bagel, or S’More, for example. And subscription services like The League are popping up as well, where users pay for a small, curated list of high-quality matches.

Be thoughtful about your profile. Maybe you’re just curious to see what this is all about, so you throw up a random selfie and dash off a silly bio. Mistake, says Eddie Hernandez, a San Francisco-based dating coach, image consultant and photographer. “Just because it's easy to set up a profile in less than 5 minutes doesn't mean you should,” he says. Most dating apps boost new user accounts, so if you’re not putting your best foot forward, you could be blowing your first, best chance to make an impression. Give it the same thought you’d give a resume for your dream job, he advises.

Flatter yourself. Save self-deprecation for the coffee date — in your profile, you want to portray yourself in the best light possible, Hernandez says. Granted, this can be tough in the limited space most apps give you, and you can assume most people are going to be making snap judgements in 5 seconds or less. The main thing to keep in mind, he says, is, “You attract what you are, not what you seek, so it's important to send the right signals to attract more of what you want and less of what you don't.” Use your photos to show off your lifestyle: hobbies, values, and interests. Dress for the type of person you want to meet – formal attire sends a much different message than fitness gear or a bikini and cutoffs (although, if you can still rock that look, more power to you!).

Don’t selfie-sabotage. Selfies can be too close to offer much detail, so Hernandez recommends a mix of close-up photos, full-body photos, and lifestyle photos. Make sure they’re clear and not blurry, and limit group photos as you should be the focus. Getting unbiased feedback on your choices can be a good idea, especially if you’re not getting the matches you want. There are online dating consultants such as who help users choose the apps and create profiles and image consultants that help clients look their best and feel confident for any occasion. During the pandemic, people have gotten a bit too comfortable in their attire and their work-from-home clothes.  

Go for quality over quantity. “There is a huge fear of scarcity in dating,” says Fulgieri. “So when folks are dating, they come at it from a place of optimization: How do I appeal to the most people?” That’s the opposite of what you want, she says. While it can feel discouraging to go day after day without a good match, in the end, all you ended is one. “Do what makes you feel the most authentically you and what makes you most comfortable,” she says. The right person will respond to that. And don’t be afraid to be picky, either. One of the best things about dating when you’re online dating is that you have a much better understanding of who you are, Fulgeri says. “The more you have an understanding of yourself and your needs, the more likely you are to be able to find someone who can meet those needs.”

Share this post


Go ahead, you deserve to

feel fantastic

Stay connected

Follow us